How to Handle First-Time Jitters with a Trans Woman

It’s one of the great milestones of your life, a dream coming true at last—you’re going to make love to a transgender woman. Don’t ruin this epic experience with all those anxieties and worries running through your mind and loins!

Here’s what men worry about when it comes to their first time, and how to cope so you can enjoy the sizzle without fizzle.

She won’t like me.

What if she’s not as turned on by you as you are by her?

The only thing you can do with this mental loop is to remember that everyone has these worries. It’s normal to worry about not being exactly what your partner wants and needs or expected. Practice accepting that your sexual needs and desires are valid and have as much place as anyone else’s.

Sex is not just for the young and perfect, and if you are young and perfect, it’s not too soon to realize that sexual pleasure is for all bodies.

Another trick to outwit these worries is to understand that you can’t control all those things. The worst case scenario is that she dislikes you and finds you a complete turn off. This is very unlikely, but if it happens, well, moving on. You can’t please everyone and there’s someone out there who will want to get naked with you!

It won’t be like I imagined.

It won’t.

Get that out of the way, and you can stop worrying about it.

Let it unfold naturally and experience what happens along the way without hoping it will conform to a strict formula of desire.

Allow it to be awkward, fun, funny, incomplete, unfinished, too fast, too shy, and imperfect. Sex never starts out perfect, and you have to start somewhere.

Get rid of all your expectations, and most of your nerves will go too.

I don’t know what to expect about her body.

You never do, getting naked with someone new.

Respect that her getting naked for you is a generous act, no matter what it reveals.

It’s okay to be nervous. Ultimately, it’s exciting to discover and explore, so try to leave expectations aside and go with the flow.

I don’t know how to please a transgender woman.

No two women are ever alike, but it won’t be that much different than how to please a woman in general. There’s no specific technique that rocks every woman’s world, but the vast majority of women appreciate attention, generosity, honesty, and patience. Let her show you how to please her. You can’t possibly know in advance.

I don’t know if I can play with or suck her cock.

If the idea of her having a cock gets you off in your private life, it’s just a matter of learning what she likes and doesn’t like and how it works for her, and you can’t possibly know any of that without experience.

The best bet is to be totally up front and say, “I’m not sure how you like to be touched” or “My experience with a penis is limited to my own, so I hope you’ll show me what feels good until it comes naturally.”

Many transgender women won’t want you to touch their cock, and many will. It won’t be the same as the cock you’re used to—your own—if she’s on hormones. It won’t be like a man’s. It will be like a woman with a penis, which is what it is.

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